Manufacture of sulpho-halogenated mono-esters and improved lubricants containing same



Patented Nov. 7, 1939 v MANUFACTURE OF SULPHO-HALOGENATED MONO-ESTERS AND IMPROVED LUBRI- CANTS CONTAINING SAME Herschel Gaston Smith, Wallingford, and Troy Lee Cantrell, Lansdowne, Pa., assignors to Gulf Oil Corporation, Pittsburgh, Pa., a corporation of Pennsylvania NoDrawing. Application June 9, 1936 Serial No. 84,386

2 Claims.

This invention relates to improved lubricants and processes of making the same; and it comprises lubricating compositions and lubricants containing small amounts of improvement agents which mitigate or retard the normal destructive action of lubricating'oil deterioration products on certain bearing surfaces, the improvement in this respect being noteworthy with even such bearing materials as alloys of cadmium with copper and silver, of cadmium with copperand nickel, of lead with copper and nickel, etc., even under relatively high temperatures, speeds and pressures, this improvement of the mineral oil being effected and its performance improved by the presence therein of a small amount of a sulpho-chlorinated mono-ester of a fatty. acid, advantageously a sulpho-chlorinated sperm oil; and it also comprises improved methodsof making such lubricants wherein unsaturated monoesters .of fatty acids, suchas sperm oil and the like, are first sulpho-chlorinated with sulphur chlorides to form substantially neutral organic sulpho-chlorinated compounds and then the sulpho-chlorinated fatty esters so obtained are 5 compounded with suitable lubricating compositions such as mineral lubricating oils, etc., in sufllcient amount to give an improved lubricant having the desired properties; all as more fully hereinafter set forth and as claimed.

Recent developments in the design of mechanical equipment for generating and transmitting power, and particularly in the automotive field,

have necessitated new bearing metals with special I properties. Among these new bearing materials 5 are binary and ternary alloys of the metals mentioned above. Cadmium-'s'ilver-copper, cadmium-nickel-copper, copper-lead-nickel, etc., alloys are in use. One ternary alloy currently used in'automobile engines is an alloy of cadmium 40 with minor amounts of both silver and copper. Under the conditions imposed by modern engineering design, these new alloy bearings are commonly subjected to more severe operating conditions than were usual in the older art: to 5 higher bearing loads, higher rubbing speeds and higher temperatures of operation. It is found that in actual use under these conditions there often develops quite serious destructive action on the bearing surface by mineral lubricating 50 oils, even by those standard commercial oils giving particularly good results with the older bearing metals under the earlier operating conditions. The destruction of the bearing metal probablyresults from action of deterioration products de- 55 veloped in the oil. An object achieved in the present invention is the production of lubricating oils improved for these newer conditions of use and which are characterized by reduction or elimination of destructive action on the newer bearing metals by deterioration products in the oil.

. We have discovered that thesulpho-chlorinated mono-esters of fatty acids, incorporated with lubricants, are capable of achieving the objects of the present invention, the sulpho-chlorinated sperm oils being particularly eifective. By

adding small amounts of such compounds to the mineral oil or lubricant, we obtain improved lu-' bricating compositions which satisfactorily lubricate alloy bearings. Incorporated in mineral oil, these compounds retard destruction of the bearing metal. Also, the film strength of the lubricant is increased, the sulpho-chlorinated compound imparting extreme pressure characteristics to the oil. The character and amount of added improvement agents, here employed, are such that the normal physical properties of the oil, such as viscosity, gravity, color, etc.,. are not substantially altered. Certain properties of the lubricant are improved. without sacrificing" the other desirable properties.

We obtain improved mineral oils and lubricants suitable for lubricating such bearings under a wide range of service conditions. The new compounded lubricant satisfactorily lubricates the new alloy bearings even under high unit pressure, high bearing speeds and high operating temperatures. When prepared from suitable mo-. tor oils, the presentimproved compositions are excellent lubricants for the modern automobile engine. They satisfactorily lubricate the bearings without any destruction of the special bear ing alloys now used, even in the presence of a free circulation of air.

Ordinarily between 0.20 and 1.00 per cent by weight on the oil, of these sulpho-chlorinated compounds, is sufficient to produce asatisfactory lubricant. However, in some cases larger amounts may be employed, for instance, with those oils of more pronounced destructive tendency. As much as 2 per cent of the improvement agent may sometimes be added with advantage.

. The particular proportions depend upon the particular sulpho-chlorinated compound and lubricating base employed and the particular type of lubricant desired.

When the larger amounts are employed, extreme pressure characteristics are also imparted to the mineral oil or lubricant. In manycases, the load carrying capacity of the lubricant may be increased by 50 to 100 per cent. Thus the addition of the sulpho-chlorinated compound gives the compound lubricant several advantageous properties. As stated ante, even a fraction of a per cent produces the desired results.

Generally, we have found that the unsaturated mono-esters of fatty acids can be readily sulphochlorinated with the various commercial sulphur chlorides under certain conditions and processed to obtain substantially neutral organic sulphochlorinated compounds. These sulpho-chlorinated mono-esters have many properties which render them advantageous as an ingredient in compounded lubricants.

The mono-esters here advantageous in preparingthe sulpho-chlorinated compounds have the following characteristic structure:

wherein n is at least 1.

They are aliphatic mono-esters unsaturated in both the acid and alcohol components thereof, that is, they contain double bonds on each side of the single ester group. These double bonds are capable of being saturated with sulphur or chlorine or both, whereby stable, substantially neutral addition products are formed. Although these mono-esters are oily compounds of aliphatic character, they are characteristically different from the ordinary fatty oils which are glycerides or tri-esters of glycerine with fatty acids. Instead, they are liquid or low melting waxes. Also, they are characteristically difierent from the ordinary parafilne waxes in that they contain an ester group.

Being characteristically diiferent from. fatty oils and from paraflinic hydrocarbons, these mono-esters yield a new type of sulpho-chlorinated products; products having properties advantageous for the present purposes. The sulphochlorinated mono-esters are readily soluble in and miscible with petroleum oils, are substantially neutral and are stable, both alone and in solution in mineral oils.

In practicing this invention either pure monoesters or mixtures thereof may be employed to prepare the sulpho-chlorinated materials. The esters or mixtures which are liquid at room temperature are advantageous. To produce high grade sulphurized products for the present purposes, we find it advantageous to use, as the starting material, mono-esters having the following properties:

Specific gravity, 60/60 F 0.878-01384 Viscosity, S. U. V., 100 F 95-110 Flash, 0. 0., F., minimum 490. Pour, F., maximum 40 Color, N. P. A. not darker than 1.5 Neutralization number, maximum 2.0 Oleic acid eq.,-percent, maximum-.. 1.0 Saponification number 125-140 Iodine number 80-90 Good grade sperm oils are readily available and are generally used in the commercial practice of this invention.

It is known that sperm oil is largely a mixture of mono-esters of the general type given ante; the esters thereof being mono-esters of ,unsaturated fatty acids of the oleic series and of monohydric alcohols of the olefin series.

Sperm oil is obtained from the head cavities and blubber of the cachelot or sperm whale (Physeter macrocephalus). The crude oil contains varying amounts of spermaceti and like solid waxes of the ester type. In refining the oil, these waxes are removed by refrigeration and pressing, to obtain the commercial sperm oils. The commercial oils are known as winter sperm oil, spring sperm oil, etc., and are substantially free of-solid waxes. The commercial sperm oil is a thin yellow liquid and when of good quality is nearly free from odor. In the present invention it is advantageous to use refined sperm oil of good quality.

In lieu of sperm oil itself (oil from the cachelot whale) other oils of the sperm oil group may be used in making the sulphurized products according to this invention. For instance, bottlenose oil (doegling oil) may be employed. It is obtained from several species of toothed cetaceans, particularly the bottlenose whale (Hyperoodon rostratum); hence the name bottlenose oil. It is so like true sperm oil in character that the commercial oil is known as arctic sperm oil. The said class of oils have certain properties in common with true sperm oil; all of these oils containing characteristic types of fatty esters.

Also in the general practice of this invention,

one or more of the mono-esters present-in sperm oil may be used; either those isolated from sperm oil or those prepared by esterifying a fatty acid of the oleic series with a monohydric alcohol which is likewise unsaturated. For instance, oleic acid may be esterified with an unsaturated monohydric alcohol which is likewise unsaturated. For instance, oleic acid may be esterified with an unsaturated monohydric alcohol having the following formula:

H H v Ho-t-(cH, ,t=c :(cH,).cHi

wherein a: is at least 1. Such alcohols may be obtained by saponifying sperm oil and recover-' ing the unsaturated alcohols thereof. These alcohols may also be obtained from other suitable sources. v Such mono-esters may be represented by the following formula:

yellowish-red heavy liquids. Commercial sulphurdichloride is a dark brownish-red liquid. However, most commercial preparations are more or less mixtures of various sulphur chlorides in equilibrium with each other; they primarily being composed of sulphur dichloride and sulphur mono-chloride, depending upon the commercial source of the preparation, and other sulphur chlorides such as sulphur tetra-chloride (S014) and sulphur tritatetra chloride (Sack) may also Specific gravity, 15/15 c 12 per cent 'of sulphur mono-chloride is sufficient.

be present. Advantageously, commercial sulphur chloride preparations having the following properties may be employed in the practice of this invention:

1.6 to in Melting point, C -78 to -80 Boiling range, C 59 to 139 Color Light yellow to dark red Sulphur, percent 31.1 to 47.4 Chlorin, percent 68.9 to 52.6

In manufacturing our improvement agents, we so react the sperm oiland like mono-esters with sulphur chloride as to avoid or restrain the formation of undesirable side-reaction products, such as oil-insoluble esters, acid or acid-developing bodies, etc. For instance, when substitution occurs to a substantial degree, much I-lCl is liberated, and the product is quite acid, is too viscous and dark in color and is insufliciently soluble in oil. Excessive reaction temperatures and amounts of sulphur chloride tend to produce such unde sirable products. The higher temperatures ordinarily give dark and undesirably viscous products. Such temperatures, particularly local-overheating, may occur if the processing is not properly effected. Excessive heavy treatment with sulphur chloride is undesirable as the products obtained are not soluble in mineral lubricating oil.

Thus we find it advantageous to employ certain controlled procedures in making our improved agents by which simple sulphur-chloride addition products readily miscible with oils are obtained. The properly made improvement agent is believed to be a simple sulpho-halogenated product or a mixture of such a product with typical sulphurized or halogenated compounds.

I'o easily obtain sulpho-chlorinated products having, the desired properties, we prefer to effect the reaction with the sulphur chloride at temperatures between 40 and 120 F. With the temperature maintained between 50 and F., while the sulphur chloride is vigorously combining with the sperm oil, particularly good results are obtained. Any suitable cooling means may be employed and vigorous agitation is used to prevent local over-heating. To further hold the temperature and reaction under control, the sulphur chloride is gradually added to the mono-ester; the rate of addition of it being such as will permit the mixture to remain within the preferred .temperature range specified, with or without external cooling, despite the exothermic heat of reaction. If no special cooling means is provided, the addition of the sulphur chloride will ordinarily require from two to five hours, depending upon the, amount used and the other factors; an additional period of two to three hours being. allowed for the reaction to complete itself after all the sulphur chloride has been added.

By adding the sulphur chloride to the sperm oil or the like, there is present, during the initial reaction, a large excess of the unsaturated comficient to completely saturate the double bonds of all the mono-ester present. Generally, 3 to 15 per cent of sulphur chloride, .by weight on the mono-ester, is satisfactory. With sperm oil, about With the other mono-esters the amount may be varied according to the particular ester and sulphur chloride employed. With the larger amounts of sulphur chloride, more viscous products are obtained. Thus we may readily control the properties of our improvement agents and obtain products having the content of combined sulphur and chlorine, the viscosity and other properties desired for the present purposes.

After the reaction is complete, the mixture may be heated under reduced pressure, say about mm. to remove unreacted sulphur chloride and any HCl that may be present. To the hot sulphochlorinated oil so obtained, powdered sodium carbonate or other solid neutralizing agent may be added with stirring and the mixture then filtered. In this way, non-volatile organic acids and residual 1101 are neutralized and removed, the salts or soaps formed being insoluble in the oil. Also, a decolorizing clay such as commercial Filtrol, may be added just prior to the said filtration to improve the color of the filtered oil. In these operations about 1 per cent of sodium carbonate and about 10 per cent of decolorizing clay, by weight on the oil, is satisfactory. A temperature of the order of F. is appropriate in these finishing steps.

In lieu of the above procedure, sometimes the reaction mixture is washed with water or a weakly alkaline aqueous solution of sodium carbonate,-

etd, the treated oil separated from the aqueous liquid and then dried. To dry the so washed oil it may be warmed and a current of air blown for finishing the sulpho-chlorinated sperm oil as it obviates any need for drying the oil.

Operating in this way, practically no hydrogen sulphide is formed and little or no HCl is evolved during the reaction. This indicates that the main reaction is one of addition and that only negligible substitution of sulphur or chloride in the mono-ester occurs. As to the small amount of HCl found in the reaction mixture and removed by the finishing procedures given ante, it is probably due to traces of moisture in the sperm oil. To prevent such decomposition of the 'sulphur chloride by.wet mono-ester, we ordinarily employ a substantially dry starting material. Advantageously the sperm oil or like mono-esters may be dried by heating them to temperatures sufficient to evaporate the moisture, say about 300 F. Such heating, also removes any volatile esters or light oils present, further improving the mono-esters for the present purposes. After this heating, the sperm oil is cooled to the minimum reaction temperature desired.

In the commercial practice of this invention, we usually heat the mono-ester (sperm oil, etc.) to about 300 F. .until the water and other volatiles are removed. It is cooled to 40-50 F. and the sulphur chloride slowly added at such a rate that the temperature, without external heating, is gradually increased to slightly below 100 F.

by the time all of the sulphur chloride has been added. The reaction mixture is then maintained at 90-100 F., by warming if necessary, until the reaction is complete. Then the reaction product is subjected to reduced pressure and heated to about C. to remove unreacted sulphur chloride and volatile by-products. After removal of such volatiles, the hot oil is treated and filtered as stated ante. In this way, we obtain sulphochlorinated mono-esters excellent for the present purposes.

For the presentpurposes, we have found that the sulpho-chlorinated mono-esters having the following properties are advantageous improvement agents:

Generally, the sulpho-chlorinated mono-esters here employed are readily miscible and compatible with petroleum oils in the percentages necessary for the present purposes. They may be incorporated with the mineral oil or lubricating base in any suitable manner. They may be dissolved in the oil by simply mixing them with the oil and slightly warming with agitation to obtain uniform lubricants. Warming to temperatures between 100 F. and 180 F. is sufficient; they being readily soluble. With the heavier and more viscous lubricating. oils this warming is advantageous since the heating lowers the viscosity of the oil, thereby facilitating the blending. Also, these agents may be first dissolved in a suitable lubricating oil to form a master batch which is subsequently blended with more lubricating oil to give a range of lubricating compositions as desired. Likewise the compounded lubricant may be converted into thickened compositions or greases in any of the usual ways. Sometimes'the improvement agent may be directly added to metal soap greases or other compounded lubricants in which a petroleum oil is the lubricating base.

In the practice of the present invention any suitable mineral lubricating oil base may be employed, either heavy or light oil. Ordinarily it is best to select a good grade of mineral lubricating oil which has suitable initial properties for the particular lubrication requirement. Then the addition of the sulpho-chlorinated mono-ester produces the additional characteristics of stability, etc., desired. That is, petroleum oils and lubricants of the usual grades; may be employed in practicing this invention. The oils having properties classifying them as .motor oils of S. A. E. 10, 20 and 30 are advantageous. Likewise, special lubricants such as are obtained by blending certain vegetable oils with the mineral oil may be improved by the addition of these agents.

The corrosion and pitting of the bearing metals by particular oils under drastic service conditions may be readily observed by visual inspection, but a special laboratory test is necessary to readily and quickly determine corrosion and pitting on a standard, comparable and reproducible basis and to readily evaluate commercial lubricants for suchalloy bearings. We have devised a satisfactory accelerated test procedure which is as follows.

An alloy bearing shell of standard dimension is submerged in 300 cc. of the oil or oil composition in a 400 cc. Pyrex beaker and heated in a thermostatically controlled oil bath to C.

In determining the loss in weight thebearing shell is washed free of oil with benzene and dried before weighing.

When determining the effectiveness of various mpr ment agents the usual procedure is to run a blank test simultaneously with the oil composition being tested, employing for that purpose a samp e of the untreated motor oil, etc.

In such tests it is advantageous to employ commercial bearing shells. These shells comprise a suitable metal backing faced with the alloy bearing metal. In the above test, the air is bubbled against the alloy bearing face. In this way, the actual bearing face is subjected to drastic conditions. By comparison of the results of such tests with actual service tests, we have found them to'be in substantial agreement as to the failure or suitability of particular series of lubricants.

In testing our lubricants, we have employed bearings of the following alloys:

1. Cadmium-silver alloy C-S '7610:

Metal Percent Cadmium s s 98 Silver s I 1 Copper l 2. Lead-copper alloy 9020 CA:

Metal Percent opper. Nickel. 2

Such alloys are used in the tests of illustrative improved lubricants given post. In such tests the loss in weight, while not extremely high when expressed as percent loss, is nevertheless very significant, as part of the bearing shell is composed of a backing of a diiferentmetal which is not attacked under the specified conditions.

The specific examples and tests given post are illustrative of detail embodiments of the present invention.

Example 1.The following example illustrates one method of preparing the improvement agent from commercial grades of sperm oil and of sulphur mono-chloride; commercial materials having the following properties being employed:

Into a suitable vessel equipped with appropriate means for agitating and for heating and cooling the reaction mixture, there are introduced 880 pounds of the above sperm oil and the oil is heated to 300 F. until any water and other volatiles present are evaporated. Then the oil is cooled to aproximately 50 F. and 120 pounds of the commercial sulphur chloride (approximately 12 percent by weight on the oil) are gradually added. The rateof introducing the sulphur chloride is so controlled as to maintain the reaction temperature between 40 and 90 F., the exothermic heat of reaction being utilized to gradually bring the temperature to about 90 F. when all the sulphur chloride has been added. Ordinarily it requires about 2 hours to so incorporate the sulphur chloride depending upon whether or not external cooling is employed. During this time the reactionmixture is vigorously agitated to prevent any local overheating. After all the sulphur chloride has been added, the reaction mixture is maintained at about 90-100 F. for a further period of 2 hours, while continuing the agitation, until the reaction is substantially complete. The hot oil product so obtained is subjected to reduced pressure, say about 100 mm. and heated to 180 F. to remove any unreacted sulphur chloride and other volatiles.

The sulpho-chlorinated oil freed of volatiles is then treated with powdered sodium carbonate. In this operation, 25 pounds of powdered sodium carbonate (about 1 per cent by weight) are stirred into the warm oil andthe mixture agi- -tated for half hour. Then this mixture is filtered under pressure to remove the salts, soaps and other insoluble matter. The filtrate is the finished improvement agent ready for use.

The improvement agent so obtained had the following properties:

Gravity, degree A. P. I 17.9 Viscosity, S. U. V.:

100 F- 887 210 F 121.6 Color, N. P. A 4.5 Chlorine, per cent 6.39 Sulphur, per cent 5.37 Neutralization number 0.57 Copper strip test Satisfactory In the above example, the amount of sulphur chloride may be varied from 6 to 14 per cent and other products obtained which have proper ties rendering them advantageous as improvement agents for lubricating compositions. The smaller amounts of sulphur chloride produce products having somewhat lower viscosities and higher gravities. Likewise other commercial sulphur chlorides and mono-esters may be employed. With the reaction temperature maintained between 50 and F. we obtain oil products having good color and other properties from any of these materials. However, if the temperature exceeds F. the products obtained are dark and undesirably viscous. With excessive temperatures undesirable side reaction products are formed.

Example 2.Into' a suitable vessel there are introduced 1000 gallons (7184 lbs.) of Pennsylvania motor oil S. A. E. 10 grade and the oil warmed to F. Then 39.4 pounds of the sulpho-chlorinated sperm oil obtained in Example 1 (0.5 per cent by weight on the motor oil) are gradually added and the mixture agitated by passing a current ofair through the oil until a uniform blend is obtained. about one hour being required. The improved motor oil is then cooled and is ready to be marketed.

Example 3.-By increasing the amount of sulpho-chlorinated sperm oil in Example 2 to 2.5 per cent by weight on the same mineral oil, we obtain another improved lubricant having the following properties:

Gravity, A. P. I 32.5 Viscosity: s. U. v.: 25 100 F 188.6 210 F 46.1

Flash, 0. C., "F 420 Fire, 0. c'., "F 490 Pour, F 0 30 Color, N. P. A 1.50 Copper strip Passes Neutralization number Nil Sulphur, per cent .01 Chlorine, per cent The improved lubricant so obtained has marked extreme pressure characteristics and is substantially non-corrosive on alloy bearings. It is an excellent lubricant for" automobile engines. 40

Example 4.--By the procedure of Example 2, employing sulpho-chlorinated sperm oil of Example 1 and a highly refined motor oil of S. A. E.

30 grade, made from Pennsylvania crude, we obtain an improved motor oil having the fol- 45 lowing composition:

Per cent by on weight 50 S. A. E. 30 grade 99 Sulpho-chlorinated sperm oil 1 When tested on the Almen testing machine, the original motor oil failed under a-load of 4000 55 pounds per square inch, whereas the improved lubricant compounded from it withstood a load of 8000 pounds per square inch.

Example 5.By, the procedure of Example 2,

employing the sulpho-chlorinated sperm oil of 0 Example 1 and a highly refined motor oil of S. A. E. 10 grade made from Pennsylvania crude,

,we obtain an improved motor oil having the following composition:

' Percent by on weight S. A. E. 10 rade 99 Sulpho-clorinated sperm oil 1 When tested by the standard laboratory test given ante, using a commercial bearing shell faced with a cadmium-silver alloy (0-5 7610), the following results were obtained in a 48 hour 75 test run on the original oil and on the improved lubricant oil.

Bearing shallwelght Original oil {g g' gggg Grams Grams Before test 36.3789 35.8239 Alter test as. 9504 35. 8263 Total change 0. 4285 +0. 0024 Bearing appearance (after test) Badtlg'egtched and No change.

. bodiments of the present invention and in practice other embodiments may be used. That is, the percentage of the agent employed may be varied as indicated, according to the particular properties desired in the final lubricant. Likewise, the lubricating'base itself may be selected according to the type of final lubricant to be produced. For instance, any of the usual greases or the usual blends of mineral and non-mineral oils may be employed as a lubricating base in making lubricants of our improved type. The addition of the improvement agent to these lubricating bases produces a like improvement in film strength and-reduces their destructiveness toward the newer bearing alloys. When incorporating the agent in a grease composition or like thickened, lubricant, mechanical agitators rather than a current of air are employed to obtain uniform mixing and blending. That is, the improvement agent and grease may be compounded in the usual mixers. such as blade mixers,

equipped with heating jackets. However, in making such greases the agent may advantageously be first incorporated with the oil base 'according to the procedure of Example 2 and then the metal soap or the thickening agents added to the improved oil, in the ordinary way to produce the desired grease compositions. In other words, the improved mineral oils of the present invention may be used in lieu of the ordinary oils in making special lubricating compositions such as greases, etc.

As stated ante, the incorporation of these improvementagents with the lubricating base pro-- duces several improvements in the final lubricant without deleteriously afiecting the desirable properties. While the exact reasons for the improvements obtained are not fully known, we are satisfied with observing and utilizing the actual improvements obtained by adding and incorpoagent with commercial initially producing effective lubricating action would normally tend to corrode said alloy bearings under said conditions, and said sulphochlorinated ester having the following properties:

Specific gravity, A. P. I 14-20 Viscosity, S. U. V., 210 F -300 Color, N. P. A 2.1-8.0 Copper strip Satisfactory Neutralization number 0.25-2.0 Sulphur, per cent 2.0-6.0 Chlorine, per cent 2.0-7.0

and being an addition product of sulphur chloride and an unsaturated aliphatic mono-ester having the following formula a H H H H n HaC(CHa)..JJ=C-(ClEl,),.C-O-C-(CH|)..-C=C-(CH:),.CHi

wherein n is 1 to 9, the amount of the sulphochlorinated mono-ester dissolved in the oil being sufiicient to efie ctively and substantially retard the destructive action on said alloy bearings which would normally occur in the absence of said sulpho-chlorinated mono-ester.

2. An improved lubricant, suitable for lubricating cadmium-silver and other special alloy bearings under relatively high bearing temperatures, speeds and pressures without corroding said alloy bearings, comprising a major proportion of a mineral oil and'between 0.2 a substantially neutral sulpho-chlorinated sperm oil dissolved therein, said mineral oil being a mineral lubricating oil which while capable of initially producing an effective lubricating action would normally tend to corrode said alloys under said conditions and said sulpho-chlorinated sperm oil having the following properties:

and being. an addition product of sulphur chloride and sperm oil, the amount of said sulphochlorinated sperm oil dissolved in the mineral oil being sufiicient to effectively and substantially retard the destructive action on said alloy bearings which would normally occur in the absence of said sulpho-chlorinated sperm oil.

HERSCHEL GASTON SMITH.

TROY LEE CANI'RELL.

and 2.5 per cent of 

